Evaluation of a PK/PBAN analog with an (E)-alkene, trans-Pro isostere identifies the Pro orientation for activity in four diverse PK/PBAN bioassays

Peptides

Volumn 30, Issue 7, 2009, Pages 1254-1259

  Nachman, Ronald J ^a   Wang, Xiaodong J ^b   Etzkorn, Felicia A ^b   Aziz, Orna Ben ^c   Davidovitch, Michael ^c   Kaczmarek, Krzysztof ^a,d   Zabrocki, Janusz ^a,d   Strey, Allison ^a   Pryor, Nan ^a   Altstein, Miriam ^c  

^a SOUTHERN PLAINS AGRICULTURAL RESEARCH CENTER   (United States)

^b VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^c VOLCANI CENTER   (Israel)

^d LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Melanization; Myotropic; Neuropeptide; PBAN; Peptidomimetic; Pheromonotropic; Pupariation

Indexed keywords

ALKENE; NEUROPEPTIDE; PHEROMONE BIOSYNTHESIS ACTIVATING NEUROPEPTIDE; PYROKININ BIOSYNTHESIS ACTIVATING NEUROPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; COCKROACH; FLY; HORMONE SYNTHESIS; MATRIX ATTACHMENT REGION; MELANOGENESIS; MOTH; PEST MANAGEMENT; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN CONFORMATION; PROTEIN DETERMINATION; PROTEIN FUNCTION; PROTEIN TARGETING;

ANIMALS; BIOLOGICAL ASSAY; COCKROACHES; DIPTERA; LARVA; MAGNETIC RESONANCE SPECTROSCOPY; MELANINS; MOLECULAR STRUCTURE; MOTHS; NEUROPEPTIDES; PEPTIDES; PHEROMONES; PROTEIN CONFORMATION; SPODOPTERA;

BLATTARIA; HELIOTHIS; HEXAPODA; LEPIDOPTERA; LEUCOPHAEA MADERAE; PELTIGERA; SARCOPHAGA BULLATA; SPODOPTERA LITTORALIS;

EID: 67349142026     PISSN: 01969781     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.peptides.2009.04.017     Document Type: Article

References (37)

1. Abernathy R.L., Nachman R.J., Teal P.E.A., Yamashita O., and Tumlinson J.H. Pheromonotropic activity of naturally-occurring pyrokinin insect neuropeptides (FXPRLamide) in Helicoverpa zea. Peptides 16 (1995) 215-219
2. Altstein M. Role of neuropeptides in sex pheromone production in moths. Peptides 25 (2004) 1491-1501
3. Altstein M., Dunkelblum E., Gabay T., Ben Aziz O., Schafler I., and Gazit Y. PBAN-induced sex-pheromone biosynthesis in Heliothis peltigera: structure, dose, and time-dependent analysis. Archives of Insect Biochemistry and Physiology 30 (1995) 307-319
4. Altstein M., Gazit Y., Ben Aziz O., Gabay T., Marcus R., Vogel Z., et al. Induction of cuticular melanization in Spodoptera littoralis larvae by PBAN/MRCH: development of a quantitative bioassay and structure function analysis. Archives of Insect Biochemistry and Physiology 31 (1996) 355-370
5. Altstein M., Gazit Y., Ben Aziz O., Zeltser I., Bhargava K., Davidovitch M., et al. Inhibition of PK/PBAN-mediated functions in insects: discovery of selective and non-selective inhibitors. Peptides 28 (2007) 574-584
6. Ben-Aziz O., Zeltser I., and Altstein M. PBAN selective antagonists: inhibition of PBAN induced cuticular melanization and sex pheromone biosynthesis in moths. Journal of Insect Physiology 51 (2005) 305-314
7. Chou P.Y., and Fasman G.D. β-Turns in proteins. Journal of Molecular Biology 115 (1977) 135-176
8. Clark B.A., and Prestwich G.D. Evidence for a C-terminal turn in PBAN. An NMR and distance geometry study. International Journal of Peptide and Protein Research 47 (1996) 361-368
9. Cook B.J., and Holman G.M. Comparative pharmacological properties of muscle function in foregut and hindgut of cockroach Leucophaea maderae. Comparative Biochemistry and Physiology C-Pharmacology Toxicology & Endocrinology 61 (1978) 291-295
10. Gade G., Hoffmann K.H., and Spring J.H. Hormonal regulation in insects: facts, gaps, and future directions. Physiological Reviews 77 (1997) 963-1032
11. Hariton A, Ben-Aziz O, Davidovitch M, Zubrzak P, Nachman RJ, Altstein M. Bioavailability of β-amino acid and C-terminally derived PK/PBAN analogs. Peptides, in press.
12. Holman G.M., Cook B.J., and Nachman R.J. Primary structure and synthesis of a blocked myotropic neuropeptide isolated from the cockroach, Leucophaea maderae. Comparative Biochemistry and Physiology C-Pharmacology Toxicology & Endocrinology 85 (1986) 219-224
13. Imai K., Konno T., Nakazawa Y., Komiya T., Isobe M., Koga K., et al. Isolation and structure of diapause hormone of the silkworm, Bombyx mori. Proceedings of the Japan Academy Series B: Physical and Biological Sciences 67 (1991) 98-101
14. Kim Y.J., Nachman R.J., Aimanova K., Gill S.J., and Adams M.E. The pheromone biosynthesis activating neuropeptide (PBAN) receptor of Heliothis virescens: identification, functional expression, and structure-activity relationships of ligand analogs. Peptides 29 (2008) 268-275
15. Matsumoto S., Kitamura A., Nagasawa H., Kataoka H., Orikasa C., Mitsui T., et al. Functional diversity of a neurohormone produced by the subesophageal ganglion: molecular identity of melanization and reddish coloration hormone and pheromone biosynthesis activating neuropeptide. J. Insect Physiol. 36 (1990) 427-432
16. Matsumoto S., Fonagy A., Kurihara M., Uchiumi K., Nagamine T., Chijimatsu M., et al. Isolation and primary structure of a novel pheromonotropic neuropeptide structurally related to leucopyrokinin from the armyworm larvae, Pseudaletia separata. Biochemical and Biophysical Research Communications 182 (1992) 534-539
17. Nachman RJ, Ben Aziz O, Davidovitch M, Kaczmarek K, Zabrocki J, Williams H, Strey A, Altstein M. A PK/PBAN analogs containing a novel dihydroimidazoline, trans-Pro mimic is a pure, selective melanotropic agonist in Egyptian cotton leaf worm (Spodoptera littoralis). Frontiers in Bioscience, in press.
18. Nachman R.J., Ben Aziz O., Davidovitch M., Zubrzak P., Isaac R.E., Strey A., et al. Biostable β-amino acid PK/PBAN analogs: agonist and antagonist properties. Peptides 30 (2009) 608-615
19. Nachman R.J., Holman G.M., and Cook B.J. Active fragments and analogs of the insect neuropeptide leucopyrokinin: structure-function studies. Biochemical and Biophysical Research Communications 137 (1986) 936-942
20. Nachman R.J., Holman G.M., Schoofs L., and Yamashita O. Silkworm diapause induction activity of myotropic pyrokinin (Fxprlamide) insect neuropeptides. Peptides 14 (1993) 1043-1048
21. Nachman R.J., Kuniyoshi H., Roberts V.A., Holman G.M., and Suzuki A. Active conformation of the pyrokinin/PBAN neuropeptide family for pheromone biosynthesis in the silkworm. Biochemical and Biophysical Research Communications 193 (1993) 661-666
22. Nachman R.J., Radel P.A., Abernathy R.L., Teal P.E.A., and Holman G.M. Mimetic analog development of the insect pyrokinin/PBAN/diapause induction (FXPRLamide) neuropeptide family. In: Suzuki A., Kataoka H., and Matsumoto S. (Eds). Molecular mechanisms of insect metamorphosis and diapause (1995), Industrial Publishing and Consulting Inc., Tokyo, Japan 97-106
23. Nachman R.J., Roberts V.A., Dyson H.J., Holman G.M., and Tainer J.A. Active conformation of an insect neuropeptide family. Proceedings of the National Academy of Science 88 (1991) 4518-4522
24. Nachman R.J., Strey A., Isaac E., Pryor N., Lopez J.D., Deng J.G., et al. Enhanced in vivo activity of peptidase-resistant analogs of the insect kinin neuropeptide family. Peptides 23 (2002) 735-745
25. Nachman R.J., Zdarek J., Holman G.M., and Hayes T.K. Pupariation acceleration in fleshfly (Sarcophaga bullata) larvae by the pyrokinin/PBAN neuropeptide family-structure-activity relationships. Annals of the New York Academy of Sciences 814 (1997) 73-79
26. Predel R., and Nachman RJ. The FXPRLamide (Pyrokinin/PBAN) peptide family, p. 207-213. In: Kastin A. (Ed). Handbook of biologically active peptides (1956), Elsevier, Amsterdam, The Netherlands 2006
27. Rafaeli A., and Jurenka R. PBAN regulation of pheromone biosynthesis in female moths. In: Blomquist G.J., and Vogt R. (Eds). Insect pheromone biochemistry and molecular biology (2003), Academic Press, New York, NY 107-136
28. Raina A.K., and Kemp T.G. A pentapeptide of the C-terminal sequence of PBAN with pheromonotropic activity. Insect Biochemistry 20 (1990) 849-851
29. Raina A.K., and Klun J.A. Brain factor control of sex-pheromone production in the female corn-earworm moth. Science 225 (1984) 531-533
30. Schoofs L., Holman G.M., Hayes T.K., Nachman R.J., and Deloof A. Isolation, primary structure, and synthesis of locustapyrokinin-a myotropic peptide of Locusta migratoria. General and Comparative Endocrinology 81 (1991) 97-104
31. Stern P.S., Yu L., Choi M.Y., Jurenka R.A., Becker L., and Rafaeli A. Molecular modeling of the binding of pheromone biosynthesis activating neuropeptide to its receptor. Journal of Insect Physiology 53 (2007) 803-818
32. Wang V.S., Kempe T.G., Raina A.K., and Mazzocchi P.H. Conformation of a biologically active C-terminal hexapeptide analog of the phreomone biosynthesis activating neuropeptide by NMR spectroscopy. International Journal of Peptide and Protein Research 43 (1994) 277-283
33. Wang X.J., Hart S.A., Xu B., Mason M.D., Goodell J.R., and Etzkorn F.A. Serine-cis-proline and serine-trans-proline isosteres: stereoselective synthesis of (Z)- and (E)-alkene mimics by Still-Wittig and Ireland-Claisen rearrangements. Journal of Organic Chemistry 68 (2003) 2343-2349
34. Wang X.J., Xu B., Mullins A.B., Neiler F.K., and Etzkorn F.A. Conformationally locked isostere of phosphoSer-cis-Pro inhibits Pin1 23-fold better than phosphoSer-trans-Pro isostere. Journal of the American Chemical Society 126 (2004) 15533-15542
35. Xu W.H., and Denlinger D.L. Molecular characterization of prothoracicotropic hormone and diapause hormone in Heliothis virescens during diapause, and a new role for diapause hormone. Insect Molecular Biology 12 (2003) 509-516
36. Žd'árek J., Myska P., Zemek R., and Nachman R.J. Mode of action of an insect neuropeptide leucopyrokinin (LPK) on pupariation in fleshfly (Sarcophaga bullata) larvae (Diptera: Sarcophagidae). Journal of Insect Physiology 48 (2002) 951-959
37. Zheng L., Njauw C.H., Lytle C., Altstein M., and Green M.M. Cloning and characterization of the pheromone biosynthesis activating neuropeptide receptor gene in Spodoptera littoralis. Gene 15 (2007) 20-30